DE3752189T2 - Behinderte tertiäre Amine enthaltende Silylierte UV-Stabilisatoren - Google Patents
Behinderte tertiäre Amine enthaltende Silylierte UV-StabilisatorenInfo
- Publication number
- DE3752189T2 DE3752189T2 DE3752189T DE3752189T DE3752189T2 DE 3752189 T2 DE3752189 T2 DE 3752189T2 DE 3752189 T DE3752189 T DE 3752189T DE 3752189 T DE3752189 T DE 3752189T DE 3752189 T2 DE3752189 T2 DE 3752189T2
- Authority
- DE
- Germany
- Prior art keywords
- carbon atoms
- branched
- straight
- radical
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 150000003512 tertiary amines Chemical class 0.000 title description 2
- 239000012963 UV stabilizer Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 73
- 239000003381 stabilizer Substances 0.000 claims abstract description 51
- 229920000642 polymer Polymers 0.000 claims abstract description 29
- 229920000620 organic polymer Polymers 0.000 claims abstract description 17
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 12
- 230000007062 hydrolysis Effects 0.000 claims abstract description 11
- 230000000087 stabilizing effect Effects 0.000 claims abstract description 7
- 239000007787 solid Substances 0.000 claims abstract description 6
- -1 alkyl radical Chemical class 0.000 claims description 46
- 239000000203 mixture Substances 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 15
- 230000008569 process Effects 0.000 claims description 15
- 150000003254 radicals Chemical class 0.000 claims description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 14
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 229910052710 silicon Inorganic materials 0.000 claims description 14
- 239000010703 silicon Substances 0.000 claims description 14
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical group CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 238000006884 silylation reaction Methods 0.000 claims description 10
- GVGCGIPIDFQMFA-UHFFFAOYSA-N 2,2,6,6-tetramethylmorpholine Chemical group CC1(C)CNCC(C)(C)O1 GVGCGIPIDFQMFA-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000004423 acyloxy group Chemical group 0.000 claims description 5
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims description 5
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 claims description 5
- 229920001577 copolymer Polymers 0.000 claims description 4
- 239000011521 glass Substances 0.000 claims description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- HYECSDJJDDNRRE-UHFFFAOYSA-N 2,2,3,5,5-pentamethylpyrrolidine Chemical compound CC1CC(C)(C)NC1(C)C HYECSDJJDDNRRE-UHFFFAOYSA-N 0.000 claims description 3
- FMRWQLAJBBKXDM-UHFFFAOYSA-N 2,2,5,5-tetramethylpyrrolidine Chemical group CC1(C)CCC(C)(C)N1 FMRWQLAJBBKXDM-UHFFFAOYSA-N 0.000 claims description 3
- 150000001336 alkenes Chemical class 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- GAURFLBIDLSLQU-UHFFFAOYSA-N diethoxy(methyl)silicon Chemical group CCO[Si](C)OCC GAURFLBIDLSLQU-UHFFFAOYSA-N 0.000 claims description 3
- 229910021485 fumed silica Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 3
- 239000012429 reaction media Substances 0.000 claims description 3
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052727 yttrium Inorganic materials 0.000 claims description 3
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 claims description 2
- 239000005909 Kieselgur Substances 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 239000004568 cement Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 238000007334 copolymerization reaction Methods 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 239000003999 initiator Substances 0.000 claims description 2
- GIWKOZXJDKMGQC-UHFFFAOYSA-L lead(2+);naphthalene-2-carboxylate Chemical compound [Pb+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 GIWKOZXJDKMGQC-UHFFFAOYSA-L 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 150000003058 platinum compounds Chemical class 0.000 claims description 2
- 229920000098 polyolefin Polymers 0.000 claims description 2
- 229910002027 silica gel Inorganic materials 0.000 claims description 2
- 239000000741 silica gel Substances 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- UHUUYVZLXJHWDV-UHFFFAOYSA-N trimethyl(methylsilyloxy)silane Chemical compound C[SiH2]O[Si](C)(C)C UHUUYVZLXJHWDV-UHFFFAOYSA-N 0.000 claims description 2
- HXZMNPWABMNDQI-UHFFFAOYSA-J tris(2,2-dibutyldodecanoyloxy)stannyl 2,2-dibutyldodecanoate Chemical compound [Sn+4].CCCCCCCCCCC(CCCC)(CCCC)C([O-])=O.CCCCCCCCCCC(CCCC)(CCCC)C([O-])=O.CCCCCCCCCCC(CCCC)(CCCC)C([O-])=O.CCCCCCCCCCC(CCCC)(CCCC)C([O-])=O HXZMNPWABMNDQI-UHFFFAOYSA-J 0.000 claims description 2
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 229920000089 Cyclic olefin copolymer Polymers 0.000 claims 1
- 125000000129 anionic group Chemical group 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- QABCGOSYZHCPGN-UHFFFAOYSA-N chloro(dimethyl)silicon Chemical compound C[Si](C)Cl QABCGOSYZHCPGN-UHFFFAOYSA-N 0.000 claims 1
- 150000002009 diols Chemical class 0.000 claims 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 1
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 claims 1
- 235000012239 silicon dioxide Nutrition 0.000 claims 1
- 239000004447 silicone coating Substances 0.000 claims 1
- 230000006641 stabilisation Effects 0.000 abstract description 4
- 238000011105 stabilization Methods 0.000 abstract description 4
- 239000000047 product Substances 0.000 description 25
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 238000009835 boiling Methods 0.000 description 11
- 238000000921 elemental analysis Methods 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000004743 Polypropylene Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 229920001155 polypropylene Polymers 0.000 description 7
- 229910002621 H2PtCl6 Inorganic materials 0.000 description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 230000015556 catabolic process Effects 0.000 description 4
- 238000006731 degradation reaction Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000003973 paint Substances 0.000 description 4
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 4
- 125000005372 silanol group Chemical group 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000005062 Polybutadiene Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 238000004949 mass spectrometry Methods 0.000 description 3
- 229920002857 polybutadiene Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- WNVSWLWUPQMHQK-UHFFFAOYSA-N 1,2,2,6,6-pentamethyl-4-prop-2-enoxypiperidine Chemical compound CN1C(C)(C)CC(OCC=C)CC1(C)C WNVSWLWUPQMHQK-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- SWZOQAGVRGQLDV-UHFFFAOYSA-N 4-[2-(4-hydroxy-2,2,6,6-tetramethylpiperidin-1-yl)ethoxy]-4-oxobutanoic acid Chemical compound CC1(C)CC(O)CC(C)(C)N1CCOC(=O)CCC(O)=O SWZOQAGVRGQLDV-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- BEIOEBMXPVYLRY-UHFFFAOYSA-N [4-[4-bis(2,4-ditert-butylphenoxy)phosphanylphenyl]phenyl]-bis(2,4-ditert-butylphenoxy)phosphane Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(C=1C=CC(=CC=1)C=1C=CC(=CC=1)P(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C BEIOEBMXPVYLRY-UHFFFAOYSA-N 0.000 description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- DRUOQOFQRYFQGB-UHFFFAOYSA-N ethoxy(dimethyl)silicon Chemical compound CCO[Si](C)C DRUOQOFQRYFQGB-UHFFFAOYSA-N 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 150000003235 pyrrolidines Chemical class 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 238000004383 yellowing Methods 0.000 description 2
- ZHBXBZGWPWKCGP-UHFFFAOYSA-N 1,2,2,5,5-pentamethyl-4-prop-2-enoxypiperidine Chemical compound CN1CC(C)(C)C(OCC=C)CC1(C)C ZHBXBZGWPWKCGP-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- UFCONGYNRWGVGH-UHFFFAOYSA-N 1-hydroxy-2,2,3,3-tetramethylpiperidine Chemical compound CC1(C)CCCN(O)C1(C)C UFCONGYNRWGVGH-UHFFFAOYSA-N 0.000 description 1
- COKOLKXVAASTJB-UHFFFAOYSA-N 1-hydroxypiperidine;hydrobromide Chemical compound Br.ON1CCCCC1 COKOLKXVAASTJB-UHFFFAOYSA-N 0.000 description 1
- BLKWTARLHMGMNW-UHFFFAOYSA-N 1-prop-1-enoxypiperidine Chemical compound CC=CON1CCCCC1 BLKWTARLHMGMNW-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- VUZNLSBZRVZGIK-UHFFFAOYSA-N 2,2,6,6-Tetramethyl-1-piperidinol Chemical compound CC1(C)CCCC(C)(C)N1O VUZNLSBZRVZGIK-UHFFFAOYSA-N 0.000 description 1
- WIXBXJIVPHLUHV-UHFFFAOYSA-N 2,2,6,6-tetramethyl-1-prop-2-enylpiperidin-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)N1CC=C WIXBXJIVPHLUHV-UHFFFAOYSA-N 0.000 description 1
- PJCGHPRUNQYHRJ-UHFFFAOYSA-N 2,2,6,6-tetramethyl-4-prop-2-enoxypiperidine Chemical compound CC1(C)CC(OCC=C)CC(C)(C)N1 PJCGHPRUNQYHRJ-UHFFFAOYSA-N 0.000 description 1
- REYQMSSIXYTZLP-UHFFFAOYSA-N 2,3,3,4-tetramethylmorpholine Chemical group CC1OCCN(C)C1(C)C REYQMSSIXYTZLP-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
- LERMQUULPSCGHK-UHFFFAOYSA-N C(C)(=O)OCCCC.C(C)(=O)OCCCC.[Sn] Chemical compound C(C)(=O)OCCCC.C(C)(=O)OCCCC.[Sn] LERMQUULPSCGHK-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 229910004721 HSiCl3 Inorganic materials 0.000 description 1
- 229910002666 PdCl2 Inorganic materials 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229940045985 antineoplastic platinum compound Drugs 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 150000001565 benzotriazoles Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- RSOILICUEWXSLA-UHFFFAOYSA-N bis(1,2,2,6,6-pentamethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)N(C)C(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)N(C)C(C)(C)C1 RSOILICUEWXSLA-UHFFFAOYSA-N 0.000 description 1
- JKJWYKGYGWOAHT-UHFFFAOYSA-N bis(prop-2-enyl) carbonate Chemical compound C=CCOC(=O)OCC=C JKJWYKGYGWOAHT-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000012084 conversion product Substances 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- NBBQQQJUOYRZCA-UHFFFAOYSA-N diethoxymethylsilane Chemical compound CCOC([SiH3])OCC NBBQQQJUOYRZCA-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- NVYQDQZEMGUESH-UHFFFAOYSA-N dimethylsilyloxy(dimethyl)silane Chemical compound C[SiH](C)O[SiH](C)C NVYQDQZEMGUESH-UHFFFAOYSA-N 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000005350 fused silica glass Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229920001903 high density polyethylene Polymers 0.000 description 1
- 239000004700 high-density polyethylene Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229920001684 low density polyethylene Polymers 0.000 description 1
- 239000004702 low-density polyethylene Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 150000002815 nickel Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 125000001339 silanediyl group Chemical group [H][Si]([H])(*)* 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0896—Compounds with a Si-H linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/544—Silicon-containing compounds containing nitrogen
- C08K5/5477—Silicon-containing compounds containing nitrogen containing nitrogen in a heterocyclic ring
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
- Y10T428/31645—Next to addition polymer from unsaturated monomers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31652—Of asbestos
- Y10T428/31667—Next to addition polymer from unsaturated monomers, or aldehyde or ketone condensation product
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31855—Of addition polymer from unsaturated monomers
- Y10T428/31938—Polymer of monoethylenically unsaturated hydrocarbon
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT21935/86A IT1197491B (it) | 1986-10-08 | 1986-10-08 | Stabilizzanti u.v. silitati contenenti ammine impedite terziarie |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3752189D1 DE3752189D1 (de) | 1998-06-18 |
| DE3752189T2 true DE3752189T2 (de) | 1998-10-08 |
Family
ID=11189060
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3752189T Expired - Fee Related DE3752189T2 (de) | 1986-10-08 | 1987-10-05 | Behinderte tertiäre Amine enthaltende Silylierte UV-Stabilisatoren |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4946880A (fr) |
| EP (1) | EP0263561B1 (fr) |
| JP (1) | JP2961541B2 (fr) |
| AT (1) | ATE166057T1 (fr) |
| CA (1) | CA1294962C (fr) |
| DE (1) | DE3752189T2 (fr) |
| ES (1) | ES2116965T3 (fr) |
| IT (1) | IT1197491B (fr) |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5089614A (en) * | 1982-04-12 | 1992-02-18 | The B. F. Goodrich Company | Polysubstituted 2-morpholones |
| IT1231221B (it) * | 1987-09-11 | 1991-11-26 | Enichem Sintesi | Cariche e pigmenti dotati anche di proprieta' stabilizzanti nei riguardi dei polimeri organici e procedimento per la loro preparazione |
| IT1218004B (it) * | 1988-05-27 | 1990-03-30 | Enichem Sintesi | Stabilizzanti uv per poli eri organici |
| US4927898A (en) * | 1988-09-06 | 1990-05-22 | Union Carbide Chemicals And Plastics Company Inc. | Polysiloxanes with sterically hindered heterocyclic moiety |
| US4895885A (en) * | 1988-09-06 | 1990-01-23 | Union Carbide Chemicals And Plastics Company Inc. | Polymer compositions stabilized with polysiloxanes containing sterically hindered heterocyclic moiety |
| FR2642764B1 (fr) * | 1989-02-03 | 1993-05-28 | Rhone Poulenc Chimie | Nouveaux composes a fonction piperidinyle et leur application dans la photostabilisation des polymeres |
| US5225113A (en) * | 1989-02-10 | 1993-07-06 | Enichem Synthesis S.P.A. | Photochromatic composition endowed with light fatigue resistance and photochromatic articles which contain it |
| IT1230711B (it) * | 1989-02-10 | 1991-10-29 | Enichem Sintesi | Composizione fotocromatica dotata di resistenza a fatica alla luce e articoli fotocromatici che la contengono. |
| IT1241082B (it) * | 1990-03-23 | 1993-12-29 | Enichem Sintesi | Metodo per la stabilizzazione di lacche e vernici e composizioni stabilizzate cosi' ottenute |
| IT1248698B (it) * | 1990-06-06 | 1995-01-26 | Ciba Geigy Spa | Composti piepridin-triazinici contenenti gruppi silossanici,atti all'impiego come stabilizzanti per materiali organici |
| US5200116A (en) * | 1990-07-23 | 1993-04-06 | Ppg Industries, Inc. | Photochromic chromene compounds |
| IT1243719B (it) * | 1990-09-18 | 1994-06-21 | Enichem Sintesi | Miscela stabilizzante per composti ad attivita' fotocromatica |
| IT1243409B (it) * | 1990-12-17 | 1994-06-10 | Ciba Geigy Spa | Composti piperidinici contenenti gruppi silenici atti all'impiego come stabilizzanti per materiali organici |
| IT1247977B (it) * | 1991-06-04 | 1995-01-05 | Ciba Geigy Spa | Stabilizzazione di materiali organici polimerici mediante l`impiego dimiscele sinergiche costituite da ammine cicliche stericamente impeditee derivati del 3-pirazolidinone o del 1,2,4,-triazolidin-3,5,-dione |
| IT1260530B (it) * | 1992-06-04 | 1996-04-09 | Enichem Sintesi | Miscele solide di stabilizzanti per polimeri |
| US5177235A (en) * | 1992-06-11 | 1993-01-05 | Ethyl Corporation | Synthesis of tetraalkylsilanes |
| IT1270870B (it) * | 1993-03-11 | 1997-05-13 | Ciba Geigy Ag | Composti polimetilipeperidinici contenenti gruppi silanici atti all'impiego come stabilizzanti per materiali organici |
| US6180011B1 (en) * | 1993-04-07 | 2001-01-30 | Enichem Synthesis S.P.A | Method for removing hydrocarbon products from water surfaces |
| US6120897A (en) * | 1993-04-15 | 2000-09-19 | Union Carbide Chemicals & Plastics Technology Corporation | Telephone cables |
| IT1269197B (it) * | 1994-01-24 | 1997-03-21 | Ciba Geigy Spa | Composti 1-idrocarbilossi piperidinici contenenti gruppi silanici atti all'impiego come stabilizzanti per materiali organici |
| IT1271131B (it) * | 1994-11-30 | 1997-05-26 | Ciba Geigy Spa | Composti piperidinici contenenti gruppi silanici come stabilizzanti per materiali organici |
| ES2223068T3 (es) * | 1995-12-18 | 2005-02-16 | General Electric Company | Mezclas de silano, de generador de radicales libres y de amina, para la reticulacion de polimeros de olefina. |
| GB9617163D0 (en) * | 1996-08-15 | 1996-09-25 | Tioxide Group Services Ltd | Treated titanium dioxide |
| FR2752582B1 (fr) * | 1996-08-21 | 2003-06-13 | Rhone Poulenc Chimie | Compositions a base de polyorganosiloxanes a groupements fonctionnels reticulables et leur utilisation pour la realisation de revetements anti-adherents |
| US5973020A (en) * | 1998-01-06 | 1999-10-26 | Rhodia Inc. | Photoinitiator composition including hindered amine stabilizer |
| FR2787462B1 (fr) * | 1998-12-22 | 2003-09-05 | Corning Sa | Capteurs de radicaux libres immobilises, preparation et utilisation |
| US6197876B1 (en) * | 1999-02-24 | 2001-03-06 | Ck Witco Corporation | Heterocyclic amine modified siloxanes |
| US20030232947A1 (en) * | 2000-11-20 | 2003-12-18 | The Procter & Gamble Company | Process for preparing an organo-modified silicone by hydrosilation reaction |
| JP4711076B2 (ja) * | 2006-04-27 | 2011-06-29 | 信越化学工業株式会社 | 光安定化基含有かご状シルセスキオキサン及びその製造方法 |
| JP2008031077A (ja) * | 2006-07-28 | 2008-02-14 | Shin Etsu Chem Co Ltd | 光安定化基含有シロキサンオリゴマー及びその製造方法 |
| ATE498645T1 (de) * | 2006-10-31 | 2011-03-15 | Bluestar Silicones France | Reaktives silanol-hals-aminosilikonpolymer mit verbesserter leistung hinsichtlich der beschichtung textiler flächengebilde |
| JP4863002B2 (ja) * | 2006-12-12 | 2012-01-25 | 信越化学工業株式会社 | シラノール化合物及びシラノール縮合体含有水溶液並びにその製造方法 |
| JP5526399B2 (ja) * | 2009-01-16 | 2014-06-18 | 日本電気株式会社 | 電極活物質、その製造方法及び二次電池 |
| US10131817B2 (en) | 2012-10-02 | 2018-11-20 | Elkem Silicones France Sas | Cationically cross-linkable/polymerizable composition comprising an iodonium borate and releasing an acceptable odor |
| JP6557977B2 (ja) * | 2015-01-15 | 2019-08-14 | Jnc株式会社 | 含窒素環化合物を含有する液晶組成物および液晶表示素子 |
| EP3345955B1 (fr) * | 2015-08-31 | 2022-04-06 | Daikin Industries, Ltd. | Composé de silane contenant un groupe perfluoro(poly)éther |
| CN107849458B (zh) * | 2015-09-04 | 2021-07-27 | Dic株式会社 | 液晶组合物及使用其的液晶显示元件 |
| JP6299932B2 (ja) * | 2015-09-04 | 2018-03-28 | Dic株式会社 | 安定剤化合物、液晶組成物および表示素子 |
| JP6780556B2 (ja) * | 2017-03-21 | 2020-11-04 | 東洋インキＳｃホールディングス株式会社 | 活性エネルギー線重合性組成物 |
| CN107235999A (zh) * | 2017-06-13 | 2017-10-10 | 江西晨光新材料有限公司 | 一种使用相转移催化剂合成含有哌啶基团的硅烷的方法 |
| CN107129574A (zh) * | 2017-06-13 | 2017-09-05 | 江西晨光新材料有限公司 | 一种合成含哌啶基团氨基硅油的合成方法 |
| JP7139995B2 (ja) * | 2019-02-25 | 2022-09-21 | 信越化学工業株式会社 | 有機ケイ素化合物、その製造方法および硬化性組成物 |
| KR20220031118A (ko) | 2019-07-15 | 2022-03-11 | 노비니움, 인크. | 장기간 전력용 케이블 성능을 연장하기 위한 실란 기능 안정제 |
| WO2021039555A1 (fr) | 2019-08-28 | 2021-03-04 | 信越化学工業株式会社 | Composition de résine durcissable à température ambiante, agent de revêtement, adhésif, agent d'étanchéité, et article |
| CN114854023A (zh) * | 2022-05-07 | 2022-08-05 | 宿迁联宏新材料有限公司 | 一种聚烯烃树脂用光稳定剂及其制备方法和应用 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB758168A (en) * | 1953-10-28 | 1956-10-03 | Midland Silicones Ltd | Organosilicon compounds |
| US4177186A (en) * | 1975-05-28 | 1979-12-04 | Ciba-Geigy Corporation | Stabilization of light-sensitive polymers |
| CH598310A5 (fr) * | 1975-05-28 | 1978-04-28 | Ciba Geigy Ag | |
| US4210578A (en) * | 1975-05-28 | 1980-07-01 | Ciba-Geigy Corporation | 4-Siloxy derivatives of polyalkylated piperidines |
| SU626092A1 (ru) * | 1976-04-06 | 1978-09-30 | Физико-Технический Институт Имени С.У.Умарова Ан Таджикской Сср | Способ стабилизации нематическх жидких кристаллов |
| IT1209543B (it) * | 1984-05-21 | 1989-08-30 | Anic Spa | Stabilizzazione di polimeri organici. |
| IT1215227B (it) * | 1984-11-13 | 1990-01-31 | Anic Spa | Procedimento per la preparazione di stabilizzanti per polimeri organici e stabilizzanti cosi'ottenuti. |
| DD234683A1 (de) * | 1985-02-13 | 1986-04-09 | Univ Dresden Tech | Verfahren zur herstellung von polymeren langzeitstabilisatoren mit hals-gruppen |
| DD234682A1 (de) | 1985-02-13 | 1986-04-09 | Univ Dresden Tech | Verfahren zur herstellung von langzeitstabilisierten polymeren mit hals-gruppen |
-
1986
- 1986-10-08 IT IT21935/86A patent/IT1197491B/it active
-
1987
- 1987-10-05 DE DE3752189T patent/DE3752189T2/de not_active Expired - Fee Related
- 1987-10-05 EP EP87201893A patent/EP0263561B1/fr not_active Expired - Lifetime
- 1987-10-05 AT AT87201893T patent/ATE166057T1/de not_active IP Right Cessation
- 1987-10-05 US US07/103,961 patent/US4946880A/en not_active Expired - Lifetime
- 1987-10-05 ES ES87201893T patent/ES2116965T3/es not_active Expired - Lifetime
- 1987-10-07 CA CA000548751A patent/CA1294962C/fr not_active Expired - Fee Related
- 1987-10-08 JP JP62252643A patent/JP2961541B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE3752189D1 (de) | 1998-06-18 |
| ES2116965T3 (es) | 1998-08-01 |
| JPS63101389A (ja) | 1988-05-06 |
| IT1197491B (it) | 1988-11-30 |
| IT8621935A0 (it) | 1986-10-08 |
| EP0263561A3 (fr) | 1990-07-25 |
| JP2961541B2 (ja) | 1999-10-12 |
| ATE166057T1 (de) | 1998-05-15 |
| US4946880A (en) | 1990-08-07 |
| EP0263561A2 (fr) | 1988-04-13 |
| EP0263561B1 (fr) | 1998-05-13 |
| CA1294962C (fr) | 1992-01-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |